Dr. Phil explores the controversial trend of older women dating much younger men. Is age really just a number? First, Pie, a 58-year-old self-admitted cougar, has been dating 24-year-old Oleg for four months — and her best friend, Terese, strongly disapproves. Could Pie be headed for heartbreak? Then, 52-year-old divorcée Bella says her relationship with 32-year-old Eddie is the best she has ever had. Eddie says he loves Bella and doesn’t mind that she’s the same age as his mother. Does this couple see a long-term future together? And, 76-year-old Aalsa — former Miss Cougar America — says after 40, men go downhill! After dating younger men for four decades, what advice does she have for fellow cougars? Tune in and decide for yourself: Can a relationship really survive a significant age gap? This show contains strong language and adult subject matter. Viewer discretion advised.